Total synthesis of northebaine, normophine, noroxymorphone enant

Details Total synthesis of northebaine, normophine, noroxymorphone enant Total synthesis of northebaine, normophine, noroxymorphone enant

1992-03-12

1997-09-16

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546149, C07D48902

Patent

active

056682859

ABSTRACT:
The invention involves a method of making key intermediates useful in the synthesis of many opiate narcotics and antagonists and agonists; and the non-opiate enantiomers thereof which have potent antitussive properties. The synthesis starts from either the natural or unnatural enantiomer of nordihydrocodeinone and produces 8, 14-dihydronorthebaine, the diketal of 7-bromonordihydrocodeinone, northebaine, norcodeinone diketal and 14-hydroxynorcodeinone intermediates without the necessity of leaving the N-nor structure. The syntheses have fewer steps than previous methods, and also have high yields.

REFERENCES:
patent: 3299072 (1967-01-01), Bartels-Keith
patent: 3896226 (1975-07-01), Fishman
patent: 4141897 (1979-02-01), Olofson et al.
patent: 4368326 (1983-01-01), Rice
patent: 4472253 (1984-09-01), Schwartz
patent: 4521601 (1985-06-01), Rice
patent: 4613668 (1986-09-01), Rice
patent: 4639520 (1987-01-01), Kavka
patent: 5071985 (1991-12-01), Andre et al.
Bartels-Keith, J. Chem. Soc.,(C), pp. 617-624 (1966).
Rice, Chemical Abstracts, vol. 101:55403t(1984) Abstract of U.S. Pat. Appl. US 564,515 Apr. 13, 1984, avail NTIS Order No. PAT-APPL-6-564 515.
Rice, J. Org. Chem., vol. 45(15), pp. 3135-3137 (Jul. 18, 1980).
Speyer, et al., Berichte, 57, pp. 1427-1430 (1924), note attached pp. 258, 262, of Bentley, The Chemistry of the Morphine Alkaloids, Oxford, Clarendon Press (1954).
Currie, et al. (I), Chemical Abstracts, vol. 56:11638b-11639h (1962).
Currie, et al. (II), Chemical Abstracts, vol. 62: 2801h-2802-2802c (1965).

Affiliated with

Also associated with

Rating

Total synthesis of northebaine, normophine, noroxymorphone enant does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Total synthesis of northebaine, normophine, noroxymorphone enant, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Total synthesis of northebaine, normophine, noroxymorphone enant will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-219680